The present invention relates to triazolone derivatives, use thereof, and intermediates therefor.
An object of the present invention is to provide compounds having excellent plant disease control activity.
As a result of the present inventors"" intensive study, it has been found that triazolone derivatives represented by the following formula [I] have excellent plant disease control activity. Thus, the present invention has been completed.
That is, the present invention provides a triazolone derivative represented by the formula [I]
wherein
R1 represents optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, halogen (chlorine, bromine, iodine or fluorine), nitro, cyano, optionally substituted C3-10 cycloalkyl, optionally substituted C4-20 cycloalkylalkyl, optionally substituted C5-10 cycloalkenyl, optionally substituted C6-20 cycloalkenylalkyl, optionally substituted C6-10 aryl, optionally substituted C7-20 arylalkyl, optionally substituted C1-9 heteroaryl, optionally substituted C2-19 heteroarylalkyl, A1xe2x80x94L1xe2x80x94, A1xe2x80x94ONxe2x95x90CA2xe2x80x94, A1xe2x80x94ONxe2x95x90C(Me)CH2ONxe2x95x90CA2xe2x80x94, A1C(A2)xe2x95x90NOCH2xe2x80x94, A1SC(A2)xe2x95x90Nxe2x80x94, A1C(xe2x95x90S)NHxe2x80x94, A1SC(xe2x95x90S)NHxe2x80x94, A1SC(SA2)xe2x95x90Nxe2x80x94, A1xe2x80x94ONxe2x95x90C(CN)xe2x80x94, A1xe2x80x94ONxe2x95x90C(Me)CH2ONxe2x95x90C(CN)xe2x80x94, or A1C(CN)xe2x95x90NOCH2xe2x80x94 (wherein L1 represents oxygen, sulfur, carbonyl, xe2x80x94OCH2xe2x80x94, xe2x80x94SCH2xe2x80x94, xe2x80x94C(xe2x95x90O)Oxe2x80x94, xe2x80x94OC(xe2x95x90O)xe2x80x94, xe2x80x94C(xe2x95x90O)OCH2xe2x80x94, xe2x80x94NHxe2x80x94, or C1-6 alkylimino; A1 and A2 are the same or different, and each represents optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted C4-20 cycloalkylalkyl, optionally substituted C5-10 cycloalkenyl, optionally substituted C6-20 cycloalkenylalkyl, optionally substituted C6-10 aryl, optionally substituted C7-20 arylalkyl, hydrogen, optionally substituted C1-9 heteroaryl, or optionally substituted C2-19 heteroarylalkyl);
R2 represents hydrogen, or C1-6 alkyl;
R3 represents C1-6 alkoxy, C1-6 alkylthio, cyano, halogen, vinyl, ethynyl, cyclopropyl, or C1-6 alkyl;
one of T, U and V represents CR4, another one represents CH or nitrogen, and the remaining one represents CR5 or nitrogen; and
W represents CR6 or nitrogen;
(wherein R4, R5 and R6 are the same or different, and each represents hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkyl, C1-6 haloalkoxy, cyano, nitro, C2-6 alkoxycarbonyl, C1-6 alkylthio, or C1-6 haloalkylthio) (hereinafter referred to as the compound of the present invention). Further, the present invention provides an agricultural or horticultural fungicide composition comprising as an active ingredient the compound of the present invention.
The present invention also provides intermediates useful for producing (a part of) the compound of the present invention, that is, an alkoxytriazolone compound represented by the formula [II-1]
wherein
R31 represents C1-6 alkyl (e.g., methyl, ethyl, etc.);
a boron compound represented by the formula [III-1]
xe2x80x83wherein both R14 bind to each other at the terminal ends thereof to represent ethylene or trimethylene (they may be substituted with one or more methyl or phenyl, respectively) (e.g., xe2x80x94C(CH3)2xe2x80x94C(CH3)2xe2x80x94, xe2x80x94CH2CH2xe2x80x94, xe2x80x94CH2CH2CH2xe2x80x94, xe2x80x94CH2xe2x80x94C(CH3)2xe2x80x94CH2xe2x80x94, xe2x80x94CH(Ph)xe2x80x94CH2xe2x80x94CH(Ph)xe2x80x94, etc.), or it represents C1-6 alkyl (e.g., methyl, ethyl, isopropyl, etc.) or hydrogen; and R2, R3, V, U, T and W are as defined above; and
a triazolone compound represented by the formula [IV]
xe2x80x83wherein R1, R2, R3, V, U, T and W are as defined above.
In the present invention, as the C1-10 alkyl of the optionally substituted C1-10 alkyl represented by R1, A1 and A2, for example, there are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, 1-methylpropyl, pentyl, 1-methylbutyl, 1-ethylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, hexyl, 1-methylpentyl, 1-ethylpentyl, 3,3-dimethylbutyl, heptyl, 3,7-dimethyloctyl, and the like.
As the C2-10 alkenyl of the optionally substituted C2-10 alkenyl represented by R1, A1 and A2, for example, there are vinyl, allyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, 2-pentenyl, 3-methyl-2-butenyl, and the like.
As the C2-10 alkynyl of the optionally substituted C2-10 alkynyl represented by R1, A1 and A2, for example, there are ethynyl, propargyl, 1-methyl-2-propynyl, 2-butynyl, and the like.
As the halogen represented by R1, there is chlorine, bromine, iodine or fluorine.
As the C3-10 cycloalkyl of the optionally substituted C3-10 cycloalkyl represented by R1, A1 and A2, for example, there are cyclopropyl, cyclopentyl, cyclohexyl, and the like.
As the C4-20 cycloalkylalkyl of the optionally substituted C4-20 cycloalkylalkyl represented by R1, A1 and A2, for example, there are cyclopropylmethyl, cyclopentylmethyl, 2-cyclopentylethyl, cyclohexylmethyl, and the like.
As the C5-10 cycloalkenyl of the optionally substituted C5-10 cycloalkenyl represented by R1, A1 and A2, for example, there are cyclopentenyl, cyclohexenyl, and the like.
As the C6-20 cycloalkenylalkyl of the optionally substituted C6-20 cycloalkenylalkyl represented by R1, A1 and A2, for example, there are cyclopentene-1-ylmethyl, cyclohexene-1-ylmethyl, and the like.
As the C6-10 aryl of the optionally substituted C6-10 aryl represented by R1, A1 and A2, for example, there are phenyl, xcex1-naphthyl, xcex2-naphthyl, and the like.
As the C7-20 arylalkyl of the optionally substituted C7-20 arylalkyl represented by R1, A1 and A2, for example, there are phenylmethyl, 2-phenylethyl, 3-phenylpropyl, 4-phenylbutyl, xcex1-naphthylmethyl, xcex2-naphthylmethyl, and the like.
As the C1-9 heteroaryl of the optionally substituted C1-9 heteroaryl represented by R1, A1 and A2, for example, there are 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1-(1,2,4-triazolyl), 3-(1,2,4-triazolyl), 4-(1,2,4-triazolyl), 2-benzothienyl, 3-benzothienyl, benzothiazol-2-yl, 2-quinolinyl, and the like.
As the C2-19 heteroarylalkyl of the optionally substituted C2-19 heteroarylalkyl represented by R1, A1 and A2, for example, there are 2-pyridylmethyl, 4-pyridylmethyl, 2-pyrimidinylmethyl, 4-pyrimidinylmethyl, 3-pyrazolylmethyl, 2-thiazolylmenthyl, 2-imidazolylmethyl, 3-(1,2,4-triazolyl)methyl, 2-quinolinylmethyl, and the like.
As the substituents of the optionally substituted C1-10 alkyl, optionally substituted C2-10 alkenyl, optionally substituted C2-10 alkynyl, optionally substituted C3-10 cycloalkyl, optionally substituted C4-20 cycloalkylalkyl, optionally substituted C5-10 cycloalkenyl, optionally substituted C6-20 cycloalkenylalkyl, optionally substituted C6-10 aryl, optionally substituted C7-20 arylalkyl, optionally substituted C1-9 heteroaryl, or optionally substituted C2-19 heteroarylalkyl represented by R1, A1 and A2, for example, there are:
halogen (chlorine, bromine, fluorine, etc.);
C1-10 alkyl (e.g., methyl, ethyl, propyl, isopropyl, butyl, isobutyl, 1-methylpropyl, pentyl, 1-methylbutyl, 1-ethylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, hexyl, 1-methylpentyl, 1-ethylpent yl, 3,3-dimethylbutyl, heptyl, 3,7-dimethyloctyl, etc.);
C3-20 trialkylsilyl (e.g. , trimethylsilyl, is triethylsilyl, etc.);
C1-10 haloalkyl (e.g., trifluoromethyl, 2,2,2-trifluoroethyl, b,1,2,2-tetrafluoroethyl, etc.);
C3-10 cycloalkyl (e.g., cyclopropyl, cyclopentyl, cyclohexyl, etc.);
C1-10 alkoxy (e.g., methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, n-pentyloxy, etc.);
C1-10 haloalkoxy (e.g., trifluoromethoxy, difluoromethoxy, bromodifluoromethoxy, chlorodifluoromethoxy, fluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, etc.);
C1-10 alkylthio (e.g., methylthio, ethylthio, n-propylthio, n-butylthio, isobutylthio, sec-butylthio, n-pentylthio, n-hexylthio, etc.);
C1-10 haloalkylthio (e.g., trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, chlorodifluoromethylthio, fluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, etc.);
C2-10 alkoxycarbonyl (e.g., methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonayl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, n-pentyloxycarbonyl, n-hexyloxycarbonyl, etc.);
phenyl; phenoxy; benzyloxy; phenoxymethyl; C1-9 heteroaryl; (C1-9 heteroaryl)methyloxy; (C1-9 heteroaryl)oxymethyl; C1-9 heteroaryloxy [wherein each of the phenyl, phenoxy, benzyloxy, phenoxymethyl, C1-9 heteroaryl, (C1-9 heteroaryl)methyloxy, (C1-9 heteroaryl)oxymethyl, and C1-9 heteroaryloxy may be substituted with one or more substituents selected from the group consisting of halogen (e.g., chlorine, etc.), C1-6 alkyl (e.g., methyl, ethyl, etc.), C1-6 alkoxy (e.g., methoxy, ethoxy, etc.), trifluoromethyl, and cyano; and examples of the C1-9 heteroaryl of the C1-9 heteroaryl, (C1-9 heteroaryl)methyloxy, (C1-9 heteroaryl)oxymethyl and C1-9 heteroaryloxy include 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 3-pyridazinyl, 4-pyridazinyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 1-(1,2,4-triazolyl), 3-(1,2,4-triazolyl), 4-(1,2,4-triazolyl), 2-benzothienyl, 3-benzothienyl, benzothiazol-2-yl, 2-quinolinyl, and the like];
methylenedioxy and difluoromethylenedioxy (each of the methylenedioxy and difluoromethylenedioxy is attached to the two adjacent carbon atoms of the aryl moiety);
hydroxyl; cyano; and nitro.
As the C1-6 alkyl represented by R2 and R31, for example, there are methyl, ethyl, and the like.
As the C1-6 alkoxy represented by R3, for example, there are methoxy, ethoxy, and the like.
As the C1-6 alkylthio represented by R3, for example, there are methylthio, ethylthio, and the like.
As the halogen represented by R3, for example, there are chlorine, bromine, iodine, fluorine, and the like.
As the C1-6 alkyl represented by R3, for example, there are methyl, ethyl, and the like.
As the halogen represented by R4, R5 and R6, for example, there are chlorine, bromine, fluorine, and the like.
As the C1-6 alkyl represented by R4, R5 and R6, for example, there are methyl, ethyl, and the like.
As the C1-6 alkoxy represented by R4, R5 and R6, for example, there are methoxy, ethoxy, and the like.
As the C1-6 haloalkyl represented by R4, R5 and R6, for example, there are trifluoromethyl, and the like.
As the C1-6 haloalkoxy represented by R4, R5 and R6, for example, there are trifluoromethoxy, difluoromethoxy, bromodifluoromethoxy, chlorodifluoromethoxy, fluoromethoxy, 2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, and the like.
P As the C2-6 alkoxycarbonyl represented by R4, R5 and R6, for example, there are methoxycarbonyl, ethoxycarbonyl, and the like.
As the C1-6 alkylthio represented by R4, R5 and R6, for example, there are methylthio, ethylthio, and the like.
As the C1-6 haloalkylthio represented by R4, R5 and R6, for example, there are trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, chlorodifluoromethylthio, fluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, and the like.
Specific examples of 6 membered aromatic ring containing T, U, V and W include benzene ring, pyridine ring and pyrimidine ring.
The compound of the present invention may be present in the form of its (E) isomer and (Z) isomer with respect to its Cxe2x95x90N bond and/or Cxe2x95x90C bond. The present invention includes both respective isomers and a mixture thereof. (The terms (E) and (Z) used herein are those used for broadly defining geometrical isomers according to Cahn-Ingold-Prelog convention.) In the compounds of the present invention, from the viewpoint of plant disease control activity, the preferred substituents are optionally substituted phenyl as R1, hydrogen as R2, and methoxy as R3.
In the compounds of the present invention, from the viewpoint of plant disease control activity, the preferred 6-membered aromatic ring moiety containing T, U, V and W is that wherein T is CMe, U is CH, V is CH and W is CH.
Among the compounds of the present invention, from the viewpoint of plant disease control activity, examples of the preferred compounds include
5-methoxy-2-methyl-4-(2-methyl-5-phenylbenzyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound of the present invention No. 6), and
4-{5-(3,3-dimethyl-1-butynyl)-2-methylbenzyl}-5-methoxy-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound of the present invention No. 526).
The compounds of the present invention can be produced according to, for example, the following Process Axe2x80x94Process E, and Process G. Further, the desired R1 can be introduced or constructed in the final step depending upon a particular R1 (e.g., Process F). In these processes, a protective group can be used for protecting a functional group from a reaction, if necessary.
As seen from the following Processes and Production Examples, among the compounds of the present invention, a part thereof, i.e., the chlorotriazoline compound represented by the formula [I-1] (Process A), the compounds represented by the formulas [I-2-1], [I-2], [I-5], [I-6], [I-5-1], [I-8], and [I-9] {Process F (Schemes 6, 7, 9, 10, and 11}, and the compound represented by the formula [I-18] {Process G (Scheme 14)} are also useful as intermediates for producing the other compounds of the present invention.
Process A: the production of the compound of the present invention wherein R3 is C1-6 alkoxy, C1-6 alkylthio, cyano, fluorine, bromine, or iodine
In this process, a chlorotriazolone compound represented by the formula [I-1]
wherein
R1, R2, T, U, V and W are as defined above, is reacted with a compound of the formula [V]
R34-M
wherein R34 is C1-6 alkoxy, C1-6 alkylthio, cyano, fluorine, bromine, or iodine; and M represents an alkali metal (e.g., sodium, potassium, lithium, cesium, etc.).
Specific examples of the compound represented by the formula [V] include sodium methoxide, sodium ethoxide, sodium thiomethoxide, sodium thioethoxide, sodium cyanate, potassium cyanate, potassium fluoride, sodium bromide, etc.
Normally, the reaction temperature of this reaction is in the range of xe2x88x9220 to 200xc2x0 C. and the reaction time is in the range of 1 to 100 hours.
Normally, in this reaction, the compound represented by the formula [V] is used at the ratio of 1 to 100 mole per 1 mole of the chlorotriazolone compound represented by the formula [I-1].
Normally, this reaction is carried out by using a solvent. Examples of the solvent include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethyl ether, tert-butyl methyl ether, etc.; aliphatic hydrocarbons such as n-hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; alcohol such as methanol, ethanol, etc.; N,N-dimethylformamide; N,N-dimethylacetamide; dimethylsulfoxide; water, etc.; or a mixture thereof.
After completion of the reaction, the reaction U mixture can be subjected to a work-up procedure such as extraction with an organic solvent, concentration, etc. to isolate the desired compound. The compound can also be purified by recrystallization, chromatography, etc.
The chlorotriazolone compound represented by the formula [I-1] can be produced, for example, as follows (Process B).
Process B: the production of the compound of the present invention wherein R3 is chlorine.
In this process, the semicarbazide compound represented by the formula [VI]
wherein R1, R2, T, U, V and W are as defined above, is reacted with triphosgene [bis(trichloromethyl)carbonate], diphosgene (trichloromethyl chloroformate) or phosgene.
Normally, the reaction temperature of this reaction is in the range of xe2x88x9220 to 150xc2x0 C. and the reaction time is in the range of 1 to 100 hours.
Normally, in this reaction, triphosgene, diphosgene or phosgene is used at the ratio of 1 to 100 mole per 1 mole of the semicarbazide compound represented by the formula [VI].
If necessary, this reaction is carried out by using a solvent. Examples of the solvent include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tert-butyl methyl ether, etc.; aliphatic hydrocarbons such as n-hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, carbon tetrachloride, monochlorobenzene, etc.; or a mixture thereof.
After completion of the reaction, the reaction mixture can be subjected to a work-up procedure such as extraction with an organic solvent, concentration, etc., to isolate the desired compound. The compound can be purified by recrystallization, chromatography, etc.
The seimicarbazide compound represented by the formula [VI] can be produced by, for example, according to the following Scheme 1. 
wherein R1, R2, T, U, V and W are as defined above; R21 represents C1-4 alkyl (e.g., methyl, ethyl, etc.); M1 represents silver or sodium; L represents a leaving group such as chlorine, bromine, iodine, p-toluenesulfonyloxy, methanesulfonyloxy, trifluoromethanesulfonyloxy, etc.; DIBAH represents diisobutylaluminum hydride; BuLi represents butyllithium; and DMF represents N,N-dimethylformamide.
The reaction for producing the compound represented by the formula [VII] by reacting the compound represented by the formula [XII] with diphosgene or phosgene can be carried out according to, for example, the process described in J. Org. Chem., 61, 3883-3884 (1996).
Process C
In this process, a triazolone compound represented by the formula [IV]
wherein
R1, R2, R3, T, U, V and W are as defined above, is reacted with a methylating agent represented by the formula [XV]
CH3xe2x80x94L2 
wherein L2 represents a leaving group such as chlorine, bromine, iodine, p-toluenesulfonyloxy, methanesulfonyloxy, trifluoromethanesulfonyloxy, OSO2OCH3, etc.
Normally, this reaction is carried out in the presence of a base. Examples of the base to be used include inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.
Normally, the reaction temperature of this reaction is in the range of xe2x88x9220 to 150xc2x0 C. and the reaction time is in the range of 1 to 100 hours.
Normally, in this reaction, the methylating agent represented by the formula [XV] and the base are used at the ratios of 1 to 5 mole, and 1 to 10 mole per 1 mole of the triazolone compound represented by the formula [IV], respectively.
If necessary, this reaction can be carried out by using a solvent. Examples of the solvent include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tert-butyl methyl ether, etc.; aliphatic hydrocarbons such as n-hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons toluene, xylene, etc.; organic bases such as pyridine, triethylamine, N-methylaniline, N,N-dimethylaniline, N,N-diethylaniline, etc.; nitrites such as acetonitrile, isobutyronitrile, etc.; N,N-dimethylformadmide; dimethylsulfoxide; water; etc., or a mixture thereof.
After completion of the reaction, the reaction mixture can be subjected to a work-up procedure such as extraction with an organic solvent, concentration, etc. to isolate the desired compound. This compound can also be purified by recrystallization, chromatography, etc.
The triazolone compound of the formula [IV] can be produced, for example, by the process according to the following Scheme 2. 
wherein R1, R2, R3, T, U, V, W and L are as defined above.
Normally, this reaction is carried out in the presence of a base (e.g., sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc.).
The compound represented by the formula [XVI] is a known compound described in, for example, JP 8-325244 A; J. Chem. Soc. Perkin I, 2644-2646 (1973); Chem. Ber. 102, 755-766 (1969); Chem. Ber. 98, 3025-3033 (1965), etc., or it can be produced according to the process described therein, or it can be produced from the compound described therein.
Among the triazolone compounds represented by the formula [IV], those wherein R3 is C1-6 alkyl or cyclopropyl can be produced according to the process of the following Scheme 3. 
wherein R33 represents C1-6 alkyl (e.g., methyl, ethyl, etc.) or cyclopropyl; and R1, R2, T, U, V and W are as defined above. Examples of the base include an aqueous solution of potassium hydroxide, etc.
Process D
In this process, a compound represented by the formula [II]
wherein R3 is as defined above (including the alkoxytriazolone compound represented by the formula [II-1]), is reacted with the compound represented by the formula [VIII] in Scheme 1.
Normally, this reaction is carried out in the presence of a base. Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, etc.; organic bases such as pyridine, 2-picoline, 4-picoline, 4-dimethylaminopyridine, quinoline, triethylamine, ethyldiisopropylamine, N, N-dimethylaniline, N, N-diethylaniline, etc.; or a mixture thereof.
Normally, the reaction temperature of this reaction is in the range of xe2x88x9220 to 150xc2x0 C. and the reaction time is in the range of 1 to 100 hours.
Normally, in this reaction, the compound represented by the formula [VIII] and the base are used at the ratios of 0.5 to 2 mole, and 0.5 to 4 mole per 1 mole of the triazolone represented by the formula [II], respectively.
If necessary, this reaction can be carried out by using a solvent. The solvent is selected according to the base used and examples of the solvent include ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tert-butyl methyl ether, etc.; aliphatic hydrocarbons such as n-hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; organic bases such as pyridine, triethylamine, N-methylaniline, N,N-dimethylaniline, N,N-diethylaniline, etc.; nitrites such as acetonitrile, isobutyronitlie, etc.; N,N-dimethylformamide; dimethylsulfoxide; water; etc., or a mixture thereof.
After completion of the reaction, the reaction mixture can be subjected to a work-up procedure such as extraction with an organic solvent, concentration, etc. to isolate the desired compound. This compound can also be purified by recrystallization, chromatography, etc.
The triazolone represented by the formula [II] is a known compound described in, for example, Chem. Ber. 102, 755-766 (1969); Chem. Ber. 98, 3025-3033 (1965); etc., or it can be produced by the process described therein or the method described in JP 8-325244 A, or it can be produced from the compound described therein.
The alkoxytriazolone compound represented by the formula [II-1] can be produced, for example, according to the following Scheme 4. 
wherein X1 represents bromine or chlorine; R31 is as defined above, R32 represents C1-6 alkyl (e.g., methyl, ethyl, etc.).
That is, the alkoxytriazolone compound represented by the formula [II-1] can be produced by cyclizing the isosemicarbazide compound represented by the formula [XXIII] or a tautomer compound thereof normally at 20 to 150xc2x0 C. normally in the presence of sodium alkoxide represented by the formula [XXIV] (e.g., sodium methoxide, sodium ethoxide, etc.), followed by treatment with an acid (e.g., hydrochloric acid, etc.).
The isosemicarbazide compound represented by the formula [XXIII] can be produced by reacting the dialkyl iminocarbonate represented by the formula [XXII] with carbazate derivative represented by the formula [XIX] normally at xe2x88x9220 to 120xc2x0 C. normally in the presence of a catalyst (e.g., protonic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, carbonic acid, acetic acid, propionic acid, pivalic acid, methanesulfonic acid, etc.).
For example, the dialkyl iminocarbonate represented by the formula [XXII] can be produced by reacting a cyanogen halide represented by the formula [XX] (cyanogen bromide or cyanogen chloride) with sodium alkoxide represented by the formula [XXIV] (e.g., sodium methoxide, sodium ethoxide, etc.) normally at xe2x88x9220 to 50xc2x0 C., followed by treatment with an acid (e.g., hydrochloric acid, etc.).
The carbazate derivative represented by the formula [XIX] can be produced by reacting alkyl chlorocarbonate represented by the formula [XVIII] with methyl hydrazine normally at xe2x88x9220 to 50xc2x0 C., if necessary, in the presence of acid trapping agent.
Process E: the production of the compound of the present invention wherein R3 is C1-6 alkyl or cyclopropyl In this process, the compound represented by the formula [XXV]
wherein R1, R2, R33, T, U, V and W are as defined above is cyclized and dehydrated.
Normally, this reaction is carried out in the presence of a base and examples of the base include inorganic bases such as potassium hydroxide, sodium hydroxide, etc.
Normally, the reaction temperature of this reaction is in the range of xe2x88x9220 to 150xc2x0 C. and the reaction time is in the range of 1 to 100 hours.
Normally, in this reaction, the base is used at the ratio of 1 to 10 mole per 1 mole of the compound represented by the formula [XXV].
If necessary, this reaction can be carried out by using a solvent. Examples of the solvent include water; ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tert-butyl methyl ether, etc.; aliphatic hydrocarbons such as n-hexane, heptane, ligroin, petroleum ether, etc.; aromatic hydrocarbons such as toluene, xylene, etc.; or a mixture thereof.
After completion of the reaction, if necessary, the reaction mixture can be acidified and then subjected to a work-up procedure such as extraction with an organic solvent, concentration, etc. to isolate the desired compound. The compound can also be purified by recrystallization, chromatography, etc.
The compound represented by the formula [XXV] can be produced, for example, according to the following process of Scheme 5. 
wherein R1, R2, R31, T, U, V and W are as defined above.
Process F
For example, there are the following F-1 to F-6.
F-1
This is the process according to Scheme 6. 
wherein X2 represents bromine or iodine; R2, R3, T, U, V and W are as defined above; and the group represented by the formula Axe2x80x94Cxe2x89xa1Cxe2x80x94H represents optionally substituted C2-10 alkynyl having the triple bond at its terminal, and A represents the residue thereof; the substituent of the C2-10 alkynyl includes that of the above optionally substituted C2-10 alkynyl represented by R1.
This reaction can be carried out in the presence of a base [for example, a tertiary amine (e.g., triethylamine, diisopropylethylamine, etc.), a secondary amine (diethylamine, etc.), a primary amine (e.g., butylamine, etc.) or the like] and a catalyst [for example, a palladium catalyst (e.g. palladium (II) acetate, tetrakis(triphenylphosphine)palladium (0), bis(triphenylphosphine)palladium (II) dichloride (PdCl2(PPh3)2, etc.) and, if necessary, copper (I) iodide and triphenylphosphine, etc.] in an aprotic polar solvent (e.g., acetonitrile, N,N-dimethylformamide, etc.) [more specifically, according to the method described in Example 1 of WO98/03464, that described in Tetrahedron Lett., 1975, 4467, that described in Synthesis, 1980, 627, or the like].
F-2
This is the process according to Scheme 7. 
wherein X represents bromine, iodine, chlorine or trifluoromethanesulfonyl; Z represents B(OR14) or SnR153; R15 represents C1-4 alkyl (e.g., methyl, ethyl, butyl, etc.); A3 represents optionally substituted C6-10 aryl or optionally substituted C1-9 heteroaryl; and R2, R3, R14, T, U, V and W are as defined above.
Normally, the reaction temperature is in the range of 20 to 120xc2x0 C., the reaction time is in the range of 1 to 24 hours and the compound represented by the formula [XXVI] is used at the ratio of 0.8 to 5 mole per 1 mole of the compound represented by the formula [I-2].
Normally, this reaction is carried out by using 0.001 to 0.1 mole of the catalyst per 1 mole of the compound represented by the formula [I-2]. Examples of the catalyst include palladium catalysts such as palladium (II) acetate, tetrakis (triphenylphosphine) palladium (0), {1,1xe2x80x2-bis(diphenylphosphino)ferrocene}dichloropalladium (II) methylene chloride complex, tris(dibenzylidene acetone)-(chloroform)-di-palladium (0) [Pd2(dba)3CHCl3], bis(triphenylphosphine)palladium (II) dichloride, etc.
If necessary, this reaction can also be carried out in the presence of a base (e.g., inorganic bases such as sodium acetate, potassium acetate, potassium carbonate, cesium carbonate, tripotassium phosphate, sodium bicarbonate, etc.), a phase-transfer catalyst (e.g., quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium bromide, etc.), a ligand (e.g., tri-tert-butylphosphine, etc.). Further, in case the compound represented by the formula [XXVII] wherein Z is SnR153, copper (II) oxide, silver (I) oxide, etc. can be used as a co-catalyst.
Normally, the reaction is carried out in a solvent. Examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, butanol, isopropanol, etc.; ether solvents such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, t-butyl methyl ether, etc.; aliphatic hydrocarbon solvents such as n-hexane, n-heptane, etc.; aromatic hydrocarbon solvents such as toluene, etc.; nitrile solvents such as acetonitrile, etc.; N,N-dimethylformamide; dimethylsulfoxide; water; etc., or a mixture thereof.
More specifically, this reaction can be carried out according to the process described in J. Org. Chem., 1997, 62, 7170-7173 [carried out in water in the presence of tetrabutylammonium bromide, a base (e.g., inorganic base such as potassium carbonate, etc.) and a catalyst (e.g., palladium (II) acetate, etc.)]; the process described in Beispiel 2 of WO96/35669 [carried out in a mixture of water and dimethoxyethane in the presence of a base (e.g., inorganic base such as sodium bicarbonate, etc.) and a catalyst (e.g., Pb(PPh3)4, etc.)]; the process described in J. Org. Chem., 1995, 60, 7508-7510; the process described in Angew. Chem. Int. Ed., 1998, 37 (24), 3387-3388; the process described in Angew. Chem. Int. Ed. Engl., 1986, 25, 508-524: or the like.
After completion of the reaction, the reaction mixture can be subjected to a conventional work-up procedure such as extraction with an organic solvent, concentration, etc. to obtain the desired compound. If necessary, the desired compound can be purified by recrystallization, chromatography, etc.
The compound represented by the formula [XXVII] is commercially available, or it can be produced by, for example, the process of the following Scheme 8. 
wherein A3, X and Z are as defined above.
For example, the reaction can be carried out by a process wherein a Grignard reagent or organic lithium compound obtained by reacting the compound represented by the formula [XXVIII] with a metal (e.g., magnesium, lithium, etc.) or an organic lithium reagent (e.g., tert-butyllithium, n-butyllithium, lithium diisopropylamide, etc.) in a solvent (e.g., diethyl ether, tetrahydrofuran etc.) is reacted with a borate (e.g., trimethyl borate, triethyl borate, triisopropyl borate, etc.), if necessary, followed by hydrolysis (more specifically, carried out according to, for example, the process described in Organometallics, 1983, 2, 1316; Liebigs Ann., 1996, 1037; Jikken Kagaku Koza, 4th Ed., Vol. 24, Organic Synthesis VI, p 80, Maruzen;, J. Am. Chem., Soc., 1958, 80, 4291-4293); a process wherein the compound represented by the formula [XXVIII] is reacted with bis(pinacolate)diborone in a solvent (e.g., dimethylsulfoxide, N,N-dimethylformamide, etc.) in the presence of a base (e.g., inorganic base such as potassium acetate, etc.) and a catalyst (e.g., {1,1xe2x80x2-bis(diphenyphosphono)ferrocene}dichloropalladium (II) methylene chloride complex, etc.), if necessary, followed by hydrolysis (more specifically, carried out according to, for example, the process described in J. Org. Chem., 1995, 60, 7508-7510); a process wherein the compound represented by the formula [XXVIII] is reacted with R153SnSnR15 (e.g., Bu3SnSnBu3, etc.) in a solvent (e.g., toluene, etc.) in the presence of a catalyst (e.g., tetrakis(triphenylphosphine)-palladium (0), etc.) (more specifically, carried out according to, for example, the process described in Chem. Letters, 1981, 829-830); or the like.
After completion of the reaction, the reaction mixture can be subjected to a conventional work-up procedure such as extraction with an organic solvent, concentration, etc. to obtain the desired compound. If necessary, the desired compound can be purified and isolated by recrystallization, distillation, chromatography, etc.
F-3
This is the process according to the following Scheme 9. 
wherein A11 represents A1 other than hydrogen, and A1, A2, R2, R3, L, T, U, V and W are as defined above.
Among the compounds represented by the formula [I-5], that wherein A2 is methyl can be produced according to, for example, the process described in J. Org. Chem., 1992, 57, 1481-1486 by reacting the compound represented by the formula [I-2] with butyl vinyl ether in the presence of a palladium catalyst, a phosphine ligand and a base, followed by acid hydrolysis.
F-4
This is the process according to the following Scheme 10. 
wherein A1, A2, R2, R3, L, T, U, V and W are as defined above.
F-5
This is the process according to the following Scheme 11. 
wherein X2, R2, R3, T, U, V and W are defined above.
This reaction can be carried out according to, for example, the process described in Synlett, 1994, 371-372.
F-6
This is the process according to the following Scheme 12. 
wherein A3, X, Z, R2, R3, T, U, V and W are as defined above.
Normally, the reaction temperature is in the range of 20 to 120xc2x0 C., the reaction time is in the range of 1 to 24 hours, and the compound represented by the formula [XXX] is used at the ratio of 1 to 5 mole per 1 mole of the compound represented by the formula [III].
Normally, in this reaction, the catalyst is used at the ratio of 0.001 to 0.1 mole per 1 mole of the compound represented by the formula [III]. Examples of the catalyst include palladium (II) acetate, tetrakis(triphenylphosphine)palladium (0), {1,1xe2x80x2-bis(diphenylphosphino)ferrocene}dichloro-palladium (II) methylene chloride complex, tris(dibenzylideneacetone)-(chloroform)-di-palladium (0) [Pd2(dba)3CHCl3], bis(triphenylphosphine)palladium (II) dichloride, etc.
If necessary, this reaction can also be carried out in the presence of a base (e.g., inorganic bases such as sodium acetate, potassium acetate, potassium carbonate, cesium carbonate, tripotassium phosphate, sodium bicarbonate, etc.), a phase-transfer catalyst (e.g., quaternary ammonium salts such as tetrabutylammonium bromide, benzyltriethylammonium bromide, etc.), a ligand (e.g., tri-tert-butylphosphine, etc.). Further, in case the compound represented by the formula [XXX] wherein A3 is SnR153, copper (II) oxide, silver (I) oxide, etc. can be used as a co-catalyst.
Normally, the reaction is carried out in a solvent. Examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, butanol, isopropanol, etc..; ether solvents such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, t-butyl methyl ether, etc.; aliphatic hydrocarbon solvents such as n-hexane, n-heptane, etc.; aromatic hydrocarbon solvents such as toluene, etc.; nitrile solvents such as acetonitrile, etc.; N,N-dimethylformamide; dimethylsulfoxide; water; etc., or a mixture thereof.
More specifically, this reaction can be carried out according to the process described in J. Org. Chem., 1997, 62, 7170-7173 [carried out in water in the presence of tetrabutylammonium bromide, a base (e.g., inorganic base such as potassium carbonate, etc.) and a catalyst (e.g., palladium (II) acetate, etc.)]; the process described in Beispiel 2 of WO96/35669 [carried out in a mixture of water and dimethoxyethane in the presence of a base (e.g., inorganic base such as sodium bicarbonate, etc.) and a catalyst (e.g., Pb(PPh3)4, etc.)]; the process described in J. Org. Chem., 1995, 60, 7508-7510; the process described in Angew. Chem. Int. Ed., 1998, 37 (24), 3387-3388; the process described in Angew. Chem. Int. Ed. Engl., 1986, 25, 508-524: or the like.
After completion of the reaction, the reaction mixture can be subjected to a conventional work-up procedure such as extraction with an organic solvent, concentration, etc. to obtain the desired compound. If necessary, the desired compound can be purified and isolated by recrystallization, distillation, chromatography, etc.
The compound represented by the formula [III] can be produced by the process represented by the following Scheme 13. 
wherein X, Z, R2, R3, T, U, V and W are as defined above.
In the reaction of Scheme 3, normally, the reaction temperature is in the range of 20 to 100xc2x0 C., the reaction time is in the range of 1 to 24 hours and the compound represented by the formula [XXIX] is used at the ratio of 1 to 5 mole pre 1 mole of the compound represented by the formula [I-2].
For example, this reaction can be carried out by a process wherein the compound represented by the formula [I-2] is reacted with bis(pinacolate)diborone, etc. in a solvent (e.g., dimethylsulfoxide, N,N-dimethylformamide, etc.) in the presence of a base (e.g., inorganic base such as potassium acetate, etc.) and a catalyst (e.g., {1,1xe2x80x2-bis(diphenyphosphono)ferrocene}dichloropalladium (II) methylene chloride complex, etc.) (more specifically, carried out according to, for example, the process described in J. Org. Chem., 1995, 60, 7508-7510); a process wherein the compound represented by the formula [I-2] is reacted with R153SnSnR15 (e.g., Bu3SnSnBu3, etc.) in a solvent (e.g., toluene, etc.) in the presence of a catalyst (e.g., tetrakis(triphenylphosphine)-palladium (0), etc.) (more specifically, carried out according to, for example, the process described in Chem. Letters, 1981, 829-830); or the like. Further, in case of the compound represented by the formula [III] wherein Z is B(OR14)2 and R14 is C1-6 alkyl, for example, the reaction can be carried out by a process wherein a Grignard reagent or organic lithium compound obtained by reacting the compound represented by the formula [I-2] with a metal (e.g., magnesium, lithium, etc.) or an organic lithium reagent (e.g., tert-butyllithium, n-butyllithium, lithium diisopropylamide, etc.) in a solvent (e.g., diethyl ether, tetrahydrofuran etc.) is reacted with a tri-C1-6 aklyl borate (e.g., trimethyl borate, triethyl borate, triisopropyl borate, etc.), if necessary, followed by hydrolysis (more. specifically, carried out according to, for example, the process described in Organometallics, 1983, 2, 1316; Liebigs Ann., 1996, 1037; Jikken Kagaku Koza, 4th Ed., Vol. 24, Organic Synthesis VI, p 80, Maruzen; J. Am. Chem., Soc., 1958, 80, 4291-4293).
After completion of the reaction, the reaction mixture can be subjected to a conventional work-up procedure such as extraction with an organic solvent, concentration, etc. to obtain the desired compound. If necessary, the desired compound can be purified by recrystallization, chromatography, etc.
Process G
This process is carried out according to the following Scheme 14. 
wherein TMS represents trimethylsilyl; and X, R1, R2, T, U, V and W are as defined above. Examples of the dehydrating agent include acetic anhydride, etc. Examples of the reducing agent include Lindlar catalyst, etc. Examples of the strong base include butyllithium, etc. Examples of the catalyst include palladium catalysts such as palladium (II) acetate, tetrakis(triphenylphosphine)palladium (0), bis(triphenylphosphine)palladium (II) dichloride (PdCl2(PPh3)2), etc. and, if necessary, copper (I) iodide and triphenylphosphine, etc.
The compound represented by the formula [XXXI] in Scheme 14, can be produced according to, for example, the following Scheme 15. 
wherein A3, L1, X, Y, R6, R7 and R8 are as defined above. Examples of the base include an aqueous solution of potassium hydroxide, etc. Examples of the methylating agent include methyl iodide-potassium carbonate, etc. Examples of the oxidizing agent include maganese dioxide, etc.
When the compound of the present invention is used as an active ingredient of an agricultural or horticultural fungicide composition, it can be used as it is without addition of any other ingredient. However, normally, it is used in admixture with solid or liquid carriers, surfactants and other supplemental agents into conventional formulations such as emulsifiable concentrates, wettable powders, suspensions, water-dispersible granules, emulsions, dusts, granules, powders, granules, and the like. These formulations normally contain as an active ingredient 0.1 to 90% by weight of the compound of the present invention based on the total weight of the formulations.
Examples of the solid carrier to be used for such formulations include finely divided powder or granules of kaolin clay, attapulgite clay, bentonite, terra alba, pyrophyllite, talc, diatomaceous earth, calcite, corn rachis powder, walnut shell powder, urea, ammonium sulfate, synthesized hydrous silicon hydroxide, etc. Examples of the liquid carrier include aromatic hydrocarbons such as xylene, methylnaphthalene, etc.; alcohol such as isopropanol, ethylene glycol, Cellosolve(trademark), etc.; ketones such as acetone, cyclohexanone, isophorone, etc.; vegetable oils such as soybean oil, cottonseed oil, etc.; dimethylsulfoxide; acetonitrile; water; etc.
Examples of the surfactant include anion surfactants such as alkylsulfate salts, aklylarylsulfonate salts, dialkylsulfosuccinate salts, salts of phosphates of polyoxyethylene alkylaryl ethers, naphthlenesulfonate formalin condensate, etc.; nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters. etc.; and the like.
Examples of the supplemental agent include ligninsulfonates, alginates, polyvinyl alcohol, gum arabic, carboxymethyl cellulose (CMC), isopropyl acid phosphate (PAP), etc.
The compound of the present invention can be applied by foliar application, soil treatment, seed disinfection, etc. as well as any other commonly utilized application method.
When the compound of the present invention is used as an active ingredient of an agricultural or horticultural fungicide composition, the dosage thereof is varied depending upon a particular kind of subject plant (crop, etc.), kind of objective plant disease, degree of disease, formulation type, application timing, weather conditions, etc. However, normally, the dosage is 0.01 to 50 g, preferably, 0.05 to 10 g per 1 are.
In case of applying emulsifiable concentrates, wettable powders, suspensions, emulsions, or the like by diluting it with water, the dosage concentration thereof is 0.0001 to 3%, preferably 0.0005 to 1%. The dusts, granules, etc. are applied as they are without dilution.
The compound of the present invention can be used as an agricultural or horticultural fungicide for fields, paddy fields, orchards, tea gardens, meadows, lawns and the like, and it is expected to enhance its fungicidal activity by using in admixture with other agricultural or horticultural fungicides. Examples of the other agricultural or horticultural fungicides which can be admixed with the compound of the present invention include azole fungicide compounds such as propiconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanoal, imazalil, flutoriafol, etc.; cyclic amine fungicide compounds such as fenpropimorph, tridemorph, fenpropidin, etc.; benzimidazole fungicide compounds such as carbendazim, benomyl, thiabendazole, thiophanate-methyl, etc.; procymidone; cyprodinil; pyrimethanil; diethofencarb; thiram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet; kresoxim-methyl; azoxystrobin; N-methyl-xcex1-methoxyimino-2-[(2,5-dimethylphenoxy)methyl]phenylacetamide, spiroxamine; quinoxyfen; fenhexamid; fenamidone (RP-407213); iprovalicarb; and the like.
The compound of the present invention can also be used in admixture with or together with other agricultural or horticultural insecticides, acaricides, nematocides, herbicides, plant growth regulators, and fertilizers.
Examples of such insecticides and/or acaricides and/or nematocides include organic phosphorous compounds such as fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate], fenthion [O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl)phosphorothioate], diazinon [O,O-diethyl O-2-isopropyl-6-methylpyridin-4-ylphosphoro-thioate], chlorpyrifos [O,O-diethyl O-3,5,6-trichloro-2-pyridylphosphorothioate], acephate [O,S-dimethylacetyl-phosphoramidothioate], methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethylphosphorothioate], disulfoton [O,O-diethyl S-2-ethylthioethylphosphorothioate], DDVP [2,2-dichlorovinyl-dimethylphosphate], sulprofos [O-ethyl O-4-(methylthio)phenyl S-propylphosphorodithioate], cyanophos [O-4-cyanophenyl O,O-dimethylphosphorothioate], dioxabenzofos [2-methoxy-4H-1,3,2-benzodioxaphosphinyn-2-sulfide], dimethoate [O,O-dimethyl S-(N-methylcarbamoylmethyl)-dithiophosphate], phenthoate [ethyl 2-dimethoxyphosphino-thioylthio(phenyl)acetate], malathion [diethyl(dimethoxyphosphinothioylthio)succinate], trichlorphon [dimethyl 2,2,2-trichloro-1-hydroxyehtylphosphpnate], azinphos-methyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-dimethylphosphorodithioate], monocrotophos [dimethyl(E)-1-methyl-2-(methylcarbamoyl)vinylphosphate], ethion [O,O,Oxe2x80x2,Oxe2x80x2-tetraethyl S,Sxe2x80x2-methylenebis-(phosphorodithioate)], fosthiazate [N-(O-methyl-S-sec-butyl)phosphorylthiazolidin-2-one], etc.; carbamate compounds such as BPMC [2-sec-butylphenylmethylcarbamate], benfuracarb [ethyl N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-xcex2-alaninate], propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-2,2-dimethyl-7-benzo[b]furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl N-methylcarbamate], methomyl [S-methyl-N-[(methylcarbamoyl)oxy]thioacetoimidate], ethiofencarb [2-(ethylthiomethyl)phenylmethylcarbamate], aldicarb [2-methyl-2-(methylthio)propionaldehyde O-methylcarbamoyloxime], oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide], fenothiocarb [S-4-phenoxybutyl-N,N-dimethylthiocarbamate], etc.; pyrethroid compounds such as ethofenprox [2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzylether], fenvalerate [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], esfenvalerate [(S)-xcex1-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], fenpropathrin [(RS)-xcex1-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS)-xcex1-cyano-3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], permethrin [3-phenoxybenzyl (1RS, 3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], cyhalothrin {(RS)-xcex1-cyano-3-phenoxybenzyl (Z)-(1RS, 3RS)-3-(2-chloro-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylate], deltamethrin [(S)-xcex1-cyano-m-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], cycloprothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], fluvalinate [xcex1-cyano-3-phenoxybenzyl N-(2-chloro-xcex1,xcex1,xcex1-trifluoro-p-tolyl)-D-valinate], bifenthrin [2-methylbiphenyl-3-ylmethyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylpropanecarboxylate], acrinathrin [(1R-{1xcex1(S*),3xcex1(Z)}]-2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoro-1-(trifluoromethyl)ethoxy-1-propenyl]cyclopropanecarboxlic acid cyano(3-phenoxyphenyl)methyl ester)], 2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl(3-phenoxybenzyl) ether, tralomethrin [(S)-xcex1-cyano-3-phenoxybenzyl (1R)-cis-3-(1,2,2,2-tetrabromoethyl)-2,2-dimethylcyclopropanecarobxylate], silafluofen [[4-ethoxyphenyl(3-(4-fluoro-3-phenoxyphenyl)propyl)-dimethylsilane]], etc.; thiadiazine derivatives such as buprofezin [(2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-triadiazinan-4-one)], etc.; nitroimidazolidine derivatives; cartap [(S,Sxe2x80x2-(2-dimethylaminotrimethylene)-bis(thiocarbamate)], nereistoxin derivatives such as thiocyclam {N,N-dimethyl-1,2,3-trithian-5-ylamine], bensultap [S,Sxe2x80x2-2-dimethylaminotrimethylene di(benzenethiosulfonate)], etc.; N-cyanoamidine derivatives such as N-cyano-Nxe2x80x2-methyl-Nxe2x80x2-(6-chloro-3-pyridylmethyl)acetamidine, etc.; chlorinated hydrocarbon compounds such as endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathepinoxide], gamma-BHC [1,2,3,4,5,6-hexachlorocyclohexane], 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol], etc.; benzoylphenylurea compounds such as chlorflazuron [1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea], teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea], flufenoxuron [1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)urea], etc.; formamidine derivatives such as amitraz [N,Nxe2x80x2-[(methylimino)dimethylidine] di-2,4-xylidine], chlordimeform [Nxe2x80x2-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide], etc.; thiourea derivatives such as diafenthiuron [N-(2,6-diisopropyl-4-phenoxyphenyl)-Nxe2x80x2-tert-butylcarbodiimide], etc.; phenylpyrazole compounds; tebufenozide [N-tert-butyl-Nxe2x80x2-(4-ethylbenzoly)-3,5-dimethylbenzohydrazide]; 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrol-3-carbonitrile; bromopropylate [isopropyl 4,4xe2x80x2-dibromobenzylate]; tetradifon [4-chlorophenyl 2,4,5-trichlorophenyl sulfone]; quinomethionate [S,S-6-methylquinoxalin-2,3-diyldithiocarbonate]; propargite [2-(4-tert-butylphenoxy)cyclohexylprop-2-yl sulfite]; fenbutatin oxide [bis[tris(2-methyl-2-phenylpropyl)tin]oxide]; hexythiazox [(4RS,5RS)-5-(4-chlorophenyl)-N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidin-3-carboxamide]; clofentezine [3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine]; pyridaben [2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one]; fenpyroximate [tert-butyl (E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminoxymethyl]benzoate], tebufenpyrad [N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-5-pyrrazolcarboxamide]; polynactin complex [tetranactin, dinactin, trinactin]; milbemectin; avermectin; ivermectin, azadirachtin [AZAD]; pyrimidifen [5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}-ethyl]-6-ethylpyrimidin-4-amine]; pymetrozine [2,3,4,5-tetrahydro-3-oxo-4-[(pyridin-3-yl)-methyleneamino]-6-methyl-1,2,4-triazine; and the like.
Examples of the plant diseases against which the compounds of the present invention exhibit controlling effects are as shown below.
rice plant: blast (Pyricularia oryzae), brown spot of rice plant (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani);
wheat, barley, etc.: powdery mildew (Erysiphe graminis), scab (Gibberella zeae), rust (Puccinia struiformis, P. graminis, P. recondita, P. hordei), snow blight (Typhula sp., Micronectriella nivalis), loose smut (Ustilago tritici, U. nuda), bunt (Tilletia caries), eye spot (Pseudocercosporella herpotrichoides), scald (Rhynchosporium secalis), specked leaf blotch (Septoria tritici), glume blotch (Leptosphaeria nodorum);
citrus: melanose (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum);
apple: blossom blight (Sclerotinia mali), canker (Valsa mali), powdery mildew (Podosphaera leucotricha), Alernaria blotch (Alternaria mali), scab (Venturia inaequalis);
pear: scab (Venturia nashicola, V. pirina), black spot (Alernaria kikuchiana), rust (Gymnosporangium haraeanum);
peach: brown rot (Sclerotina cinerea), (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.);
grape: anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), powdery mildew (Uncinula necator) , rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii), downy mildew (Plasmopare viticola);
persimmon: anthracnoce (Gloeosporium kaki), leaf spot (Cercospora kaki, Mycosphaerella newae);
cucumber, melon, etc.: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (Mycosphaerella melonis), Fusarium wilt (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), late blight (Phytophthora sp.), damping-off (Pythium sp.);
tomato: early blight (Alternaria solani), leaf mold (Cladosporium fulvum), late blight (Phytophthora infestans);
eggplant: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);
Cruciferae vegetable: Alternaria leaf spot (Alternaria japonica), white spot (Cercosporella brassicae);
Welsh onion: rust (Puccinia allii);
soybean: purple stain (Cercospora kikuchii), Sphaceloma scab (Elsinoe glycines), pod and stem blight (Diaporthe phaseolorum var. sojae);
kidney bean: anthracnose (Colletotrichum lindemthianum);
peanut: leaf spot (Cercospora personata), brown leaf spot (Cercospora arachidicola);
pea: powdery mildew (Erysiphe pisi);
potato: early blight (Alernaria solani), late blight (Phytophthora infestans);
strawberry: powdery mildew (Sphaerotheca humuli);
tea: net blister blight (Exobasidium reticulatum), white scab (Elsinoe leucospila);
tobacco: brown spot (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae);
beet: Cercisoira leaf spot (Cercospora beticola);
rose: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
chrysanthemum: leaf blight (Septoria chrysanthemi-indici), rust (Puccinia horiana);
various crops: gray mold (Botrytis cinerea), stem rot (Sclerotinia sclerotiorum); and the like.